2,4-Dichloro-6-methoxyquinoline → 4-(4-Chloro-6-methoxyquinolin-2-yl)benzonitrile

HRID 55788Notes

Reaction equation

HRID 55788 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].Cl[C:13]1[CH:22]=[C:21]([Cl:23])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:24][CH3:25])[CH:19]=2)[N:14]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[Cl:23][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:24][CH3:25])[CH:19]=2)[N:14]=[C:13]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:22]=1

Participants

5

Reactant 2

HCID 9483562,4-Dichloro-6-methoxyquinolineHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 669800504-(4-Chloro-6-methoxyquinolin-2-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Followed Scheme 2, Step 1 starting from 4-cyanophenylboronic acid and 2,4-dichloro-6-methoxyquinoline, where the solvent used was DMF, and the catalyst used was Pd(PPh3)4. The mixture was heated to 100° C. for 3 h, allowed to cool, and then poured into ice water. The resulting solid was isolated by filtration, washed with water, and dried followed by recrystallization from methanol to give the desired product.

Workup

  1. temperatureto cool
  2. customThe resulting solid was isolated by filtration
  3. washwashed with water
  4. customdried
  5. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-97998844ef324c87acdbf1f359fa7e10
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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